A Direct, Selective, and General Method for Reductive Deamination of Primary Amines

Journal of the American Chemical Society

Volumn 100, Issue 1, 1978, Pages 341-342

  Doldouras, G A ^a   Kollonitsch, J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000799014     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00469a088     Document Type: Article

References (9)

1. a). Transformation of some unsubstituted primary amines into the corresponding hydrocarbons by reaction with difluoroamine HNF2 has already beer described: C. L. Bumgardner, K. J. Martin, and J. P. Freeman, J. Am. Chem. Soc., 85, 97 (1963). The need for vacuum-line techniques and the explosive nature of HNFj apparently discouraged development of this very interesting reaction.
2. A. Nickon and A. S. Hill (J. Am. Chem. Soc., 86, 1152 (1964). showed that sulfonamides of primary amines give alkanes and arenes by treatment with 8-58 mol of hydroxylamine-O-sulfonic acid in boiling strongly basic aqueous systems. Also, N,N-disulfonimides, derived from unhindered amines, provide alkanes upon displacement with hydride anions at 150 °C: R. O. Hutchins, F. Cistone, B. Goldsmith, and P. Heuman, J. Org. Chem., 40, 2018 (1975).
3. J. ten Broeke, E. J. Grabowski, L. M. Flataker, M. H. Fisher, and A. A. Patchett, U.S. Patent 4 033 968 (1977).
4. R. Gosl and A. Meuwsen, Chem. Ber., 92, 2521 (1959).; Org. Synth., 43, 1 (1963).
5. R. Appel and O. Büchner, Angew. Chem., Int. Ed. Engl., 1, 332 (1962).
6. a). D. M. Lemal, “Nitrenes”, W. Lwowski, Ed., Interscience, New York, N.Y., 1970, p 347;
7. E. M. Kosower, Acc. Chem. Res., 4, 193 (1971).
8. D. F. Reinhold, R. A. Firestone, W. A. Gaines, J. M. Chemerda, and M. Sletzinger, J. Org. Chem., 33, 1209 (1968).
9. For the closely related L-(+). -3,4-dimethoxy-α-methylhydrocinnamic acid, [α]D 27.5° (c 4, in CHCI3)., see A. W. Schrecker, J. Org. Chem., 22, 33 (1957).